Side reactions in the SPPS of Cys-containing peptides
| dc.contributor.author | Stathopoulos, P. | en |
| dc.contributor.author | Papas, S. | en |
| dc.contributor.author | Pappas, C. | en |
| dc.contributor.author | Mousis, V. | en |
| dc.contributor.author | Sayyad, N. | en |
| dc.contributor.author | Theodorou, V. | en |
| dc.contributor.author | Tzakos, A. G. | en |
| dc.contributor.author | Tsikaris, V. | en |
| dc.date.accessioned | 2015-11-24T16:47:14Z | |
| dc.date.available | 2015-11-24T16:47:14Z | |
| dc.identifier.issn | 1438-2199 | - |
| dc.identifier.uri | https://olympias.lib.uoi.gr/jspui/handle/123456789/9154 | |
| dc.rights | Default Licence | - |
| dc.subject | Alkylation | en |
| dc.subject | Amino Acid Sequence | en |
| dc.subject | Amino Acids/chemistry | en |
| dc.subject | Chromatography, High Pressure Liquid | en |
| dc.subject | Cysteine/*chemistry | en |
| dc.subject | Fluorenes/chemistry | en |
| dc.subject | Molecular Structure | en |
| dc.subject | Oligopeptides/*chemical synthesis/chemistry/isolation & purification | en |
| dc.subject | Solid-Phase Synthesis Techniques | en |
| dc.subject | Spectrometry, Mass, Electrospray Ionization | en |
| dc.title | Side reactions in the SPPS of Cys-containing peptides | en |
| heal.abstract | Alkylation of sensitive amino acids during synthesis of biologically important peptides is a common and well-documented problem in Fmoc-based strategy. Herein, we probed for the first time an unexpected S-alkylation of Cys-containing peptides that occur during the final TFA cleavage of peptides from the Wang solid support. Through a battery of approaches (NMR, UV and LC-MS) the formed by-product was assigned as the alkylation of the cysteine sulfydryl group by the p-hydroxyl benzyl group derived from the acidic Wang linker decomposition. Factors affecting this side reaction were monitored and a protocol that minimizes the presence of the by-product is reported. | en |
| heal.access | campus | - |
| heal.fullTextAvailability | TRUE | - |
| heal.identifier.primary | 10.1007/s00726-013-1471-7 | - |
| heal.identifier.secondary | http://www.ncbi.nlm.nih.gov/pubmed/23459989 | - |
| heal.identifier.secondary | http://download.springer.com/static/pdf/450/art%253A10.1007%252Fs00726-013-1471-7.pdf?auth66=1383208755_e3e97b30f7effffdf03851390978701e&ext=.pdf | - |
| heal.journalName | Amino Acids | en |
| heal.journalType | peer reviewed | - |
| heal.language | en | - |
| heal.publicationDate | 2013 | - |
| heal.publisher | Springer-Verlag | en |
| heal.recordProvider | Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας | el |
| heal.type | journalArticle | - |
| heal.type.el | Άρθρο Περιοδικού | el |
| heal.type.en | Journal article | en |
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